Tetrahedron p. 1979 - 1984 (1985)
Update date:2022-08-05
Topics:
Foehlisch, Baldur
Herrscher, Otto
8-Oxabicyclo<3.2.1>oct-6-en-3-ones (5), easily available by <4+3> cycloaddition, were epoxidised at the C=C double bond.The 3,9-dioxatricyclo<3.3.1.02,4>nonan-7-ones (6) thus obtained are rearranged on treatment with sodium ethoxide in ethanol to form 3-hydroxybenzaldehydes (8a-d) and 3-hydroxy-2,4,5-trimethylacetophenone (8e) in good yields.As intermediates of these rearrangements, 8-hydroxy-6-oxatricyclo<3.2.1.02,7>octan-3-ones are postulated; the trimethyl derivative 7g and the 6-carba-derivatives 4a,b could be isolated.
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